A New Phenylpropanoid Glycoside: Serratumoside A from Clerodendrum serratum

In the previous papers"', we have reported some chemical constituents fromClerodendrum serratum var. amplerghlium Moldenke. A continuation of our studies onthe same plant led to the isolation of a new phenylpropanoid, serratumoside A (l), whichis reported in this paper.Serratumoside A (l) with three known phenylpropanoid glycosides identified asacteoside', mwtinoside' and myricoside', respectively, were isolated from the Cserratum. Compound I was isolated as a brown amorphous powder, laly …     

苷类研究ⅩⅩⅥ: 苯丙素苷Eutigoside A的合成研究

首次报道了苯丙素苷类化合物EutigosideA,即1-O-[2-(4-羟基苯基)乙基]-6-O-(E)-香豆酰基-β-D-吡喃葡萄糖的全合成。从四乙酰溴代葡萄糖出发,经过成苷、脱乙酰基两步反应,制备了2-对烯丙氧基苯基-β-D-吡喃葡萄糖苷(3),采用酰氯法在低温下将对乙酰氧基肉桂酰基引入化合物3的葡萄糖6位,再经过脱烯丙基、脱乙酰基两步,便顺利地合成了天然苯丙素苷EutigosideA。以化合物3为原料,经过对葡萄糖4,6位亚苄基化、2,3位乙酰化、4,6位脱亚苄基、选择性6位乙酰化及4位引入对乙酰氧基肉桂酰基等五步反应,得到了保护的苯丙素苷(OsmanthusideA(10);但在NH~3/MeOH条件下脱乙酰基时,化合物10中的香豆酰基从葡萄糖的4位迁移至6位,最终又得到了EutigosideA。     

Two New Megastigmane Glycosides and a New Iridoid Glycoside from Gelsemium elegans

Two new megastigmane glycosides, eleganosides A and B ( 1 and 3 , resp.), and one new iridoid glycoside, gouwenoside A ( 4 ), together with two known compounds, foliasalacioside B₁ ( 2 ) and loganin ( 5 ), were isolated from the aerial parts of Gelsemium elegans (Gardn. et Champ.) Benth. (Loganiaceae). Their structures were elucidated by spectroscopic methods including 1D‐ and 2D‐NMR techniques. The absolute configuration of 1 was determined by CD spectroscopy.     

Hypoglycemic and Anti-Inflammatory Effects of Triterpene Glycoside Fractions from Aeculus hippocastanum Seeds

Horse chestnut (Aesculus hippocastanum L.)-derived drugs have shown their potential in biomedical applications. The seed of A. hippocastanum contains various kinds of chemical compounds including phenolics, flavonoids, coumarins, and triterpene saponins. Here, we investigated the chemical components in A. hippocastanum L. grown in Uzbekistan, which has not yet been studied in detail. We identified 30 kinds of triterpene saponins in an extract of A. hippocastanum L. Classifying extracted saponins into eight fractions, we next studied the hypoglycemic and the anti-inflammatory activities of escin and its derivatives through in vivo experiments. We came by data indicating the highest (SF-1 and SF-2) and the lowest (SF-5 and SF-8) antidiabetic and anti-inflammatory effects of those eight fractions. These results imply the prospective use of A. hippocastanum L. grown in Uzbekistan in the production of pharmaceutical drugs to treat diabetes and inflammation.     

5-Dodecanolide,a Compound Isolated from Pig Lard,Presents Powerful Anti-Inflammatory Properties

Background: Pork lard (PL) is traditionally used as an anti-inflammatory agent. We propose to demonstrate the anti-inflammatory properties of PL, and elucidate which compounds could be responsible for the anti-inflammatory effects. Methods: The anti-inflammatory effects of PL were tested in a rat model of zymosan-induced hind paw inflammation. Further, the hydroalcoholic extract from PL was obtained, the composition analyzed, and the anti-inflammatory activity of the extracts and isolated components assayed using immune cells stimulated with lipopolysaccharide (LPS). Results: Applying the ointment on the inflamed rat feet reduced the foot diameter, foot weight, and activities of antioxidant enzymes and inflammatory markers of circulating neutrophils. The main components of the hydroalcoholic extract were 5-dodecanolide, oleamide, hexadecanoic acid, 9-octadecenoic acid, hexadecanamide, and resolvin D1. Conclusions: PL reduces the immune response in an animal model stimulated with zymosan. Hydroalcoholic PL extract and its components (5-Dodecanolide, Oleamide, and Resolvin D1) exerted an anti-inflammatory effect on LPS-stimulated neutrophils and peripheral mononuclear cells reducing the capability to produce TNFα, as well as the activities of antioxidant and pro-inflammatory enzymes. These effects are attributable to 5-dodecanolide, although the effects of this compound alone do not reach the magnitude of the anti-inflammatory effects observed by the complete hydroalcoholic extract.     

A New Prenylated Isoflavone and a New Flavonol Glycoside from Flemingia philippinensis

A new prenylated isoflavonoid, flemiphilippinin G ( 1 ), and a new flavonol glycoside, flemiphilippininside ( 2 ), along with eleven known isoflavonoids were obtained from the roots of Flemingia philippinensis (Merr. et Rolfe) Li . Their structures were elucidated on the basis of spectroscopic data. The in vitro cytotoxicities of compounds 1 – 13 against MCF‐7, A549, and Hep‐G2 cell lines were determined by using the MTT (=3‐(4,5‐dimethylthazol‐2‐yl)‐2,5‐diphenyl‐2H‐tetrazolium bromide) colorimetric assay, and their antioxidant activities were evaluated by ferric‐reducing antioxidant power (FRAP) method. Compound 1 exhibited significant cytotoxicity against all the tested cell lines with IC₅₀ values of 4.8–7.3 μM , and compound 2 was found to be inactive. Both compounds 1 and 2 showed weak antioxidant activities with FRAP values of 110±15 and 124±16 μmol/g, respectively.     

Chlorophytoside A, a New Labdane Diterpene Glycoside from Chlorophytum laxum

A new labdane-type diterpene glycoside 1 , chlorophytoside A, had been isolated from Chlorophytum laxum R.Br. The structure had been elucidated as (10S)-6α-hydroxylabda-8,13-dien-15,16-olide 3R-O-β-D-glucopyranoside on the basis of chemical and spectroscopic data.     

Dissectol A,A Novel Monoterpene Glycoside from Incarvillea dissectifoliola

Dissectol A,a novel monoterpene glycoside was isolated from the methanol part of the 95% EtOH extract of Incarvillea dissecfoliola and its structure was determined by 1D and 2D NMR data.     

Anti-Inflammatory and Anti-Platelet Properties of Lipid Bioactives from Apple Cider By-Products

The valorization of food industry by-products as sources of bioactive compounds is at the forefront of research in functional foods and nutraceuticals. This study focuses on bioactives of apple cider by-products (ACBPs) with putative cardio-protective properties. Total lipids (TLs) were extracted from ACBPs of apple varieties that are low (ACBP1), medium (ACBP2), and high (ACBP3) in tannins and were further separated into polar lipids (PLs) and neutral lipids (NLs). The functionality of these lipid extracts and of their HPLC-derived lipid fractions/PL subclasses were assessed in vitro against human platelet aggregation induced by the thrombotic and inflammatory platelet agonists platelet-activating factor (PAF) and adenosine diphosphate (ADP). The fatty acid profile of PLs and their most bioactive lipid fractions were evaluated by GC–MS analysis. The PL extracts exhibited higher specificity against the PAF-induced platelet aggregation compared to their anti-ADP effects, while TL and NL showed lower bioactivities in all ACBPs. HPLC analysis unveiled that the most bioactive PL from all ACBPs were those in PL fraction 3 containing phosphatidylcholines (PCs). PLs from all ACBPs and their PC bioactives were rich in polyunsaturated fatty acids (PUFAs) and especially in the essential omega-6 (n-6) linoleic acid (LA) and omega-3 (n-3) alpha linolenic acid (ALA), with favorably low values of the n-6/n-3 PUFA ratio, thus providing a rationale for their higher anti-inflammatory bioactivities. Within this study, highly bioactive PL compounds with strong anti-inflammatory and anti-platelet properties were identified in ACBPs, which can be potentially utilized for producing cardio-protective functional foods and/or nutraceuticals.     

A Diterpene, a Flavonol Glycoside, and a Phytosterol Glycoside from Securidaca longipedunculata and Entada abyssinica

Summary.  The MeOH extract of the stem bark of Entada abyssinica and of the leaves and stem bark of Securidaca longipedunculata yielded a diterpene, a flavonol glycoside, and a phytosterol glycoside. Their structures were established on basis of NMR spectroscopic analysis; the complete ¹³C and ¹H assignment of the compounds was achieved by means of 2D NMR studies. Received October 13, 1999. Accepted November 3, 1999     

17-Dehydroxyholothurin A, a New Sulfated Triterpene Glycoside from Sea Cucumber Holothuna impatiens

A new sulfated triterpene glycoside named as 17-dehydroxyholothurin A 1 was isolated from the sea cucumber Holothuria impatiens. Its structure was elucidated on the basis of spectroscopic data (2D NMR and MS) and chemical evidence. Compound 1 showed cytotoxic activity against cancer cell lines MKN-28, MFC-7, KB, HL-60 and Hep G2 with IC50 values of 1.98, 4.53, 2.01, 4.69 and 2.80×10-6 mol/L, respectively.     

A Novel Phenylpropanoid-substituted Catechin Glycoside and a New Dihydrochalcone from Sarcandra glabra

Sarcandra glabra (Thunb.) Nakai [Chloranthus glaber (Thunb.) Makino] (Chloranthace-ae) grows in the southern part of China, Japan and southeastern Asia. It is cultivated inJapan as ornamental plant. The whole plant has been used as an antibacterial and an…     

Production of Verbascoside,Isoverbascoside and Phenolic Acids in Callus,Suspension, and Bioreactor Cultures of Verbena officinalis and Biological Properties of Biomass Extracts

Callus, suspension and bioreactor cultures of Verbena officinalis were established, and optimized for biomass growth and production of phenylpropanoid glycosides, phenolic acids, flavonoids and iridoids. All types of cultures were maintained on/in the Murashige and Skoog (MS) media with 1 mg/L BAP and 1 mg/L NAA. The inoculum sizes were optimized in callus and suspension cultures. Moreover, the growth of the culture in two different types of bioreactors—a balloon bioreactor (BB) and a stirred-tank bioreactor (STB) was tested. In methanolic extracts from biomass of all types of in vitro cultures the presence of the same metabolites—verbascoside, isoverbascoside, and six phenolic acids: protocatechuic, chlorogenic, vanillic, caffeic, ferulic and rosmarinic acids was confirmed and quantified by the HPLC-DAD method. In the extracts from lyophilized culture media, no metabolites were found. The main metabolites in biomass extracts were verbascoside and isoverbascoside. Their maximum amounts in g/100 g DW (dry weight) in the tested types of cultures were as follow: 7.25 and 0.61 (callus), 7.06 and 0.48 (suspension), 7.69 and 0.31 (BB), 9.18 and 0.34 (STB). The amounts of phenolic acids were many times lower, max. total content reached of 26.90, 50.72, 19.88, and 36.78 mg/100 g DW, respectively. The highest content of verbascoside and also a high content of isoverbascoside obtained in STB (stirred-tank bioreactor) were 5.3 and 7.8 times higher than in extracts from overground parts of the parent plant. In the extracts from parent plant two iridoids—verbenalin and hastatoside, were also abundant. All investigated biomass extracts and the extracts from parent plant showed the antiproliferative, antioxidant and antibacterial activities. The strongest activities were documented for the cultures maintained in STB. We propose extracts from in vitro cultured biomass of vervain, especially from STB, as a rich source of bioactive metabolites with antiproliferative, antioxidant and antibacterial properties.     

A Report on Multi-Target Anti-Inflammatory Properties of Phytoconstituents from Monochoria hastata (Family: Pontederiaceae)

This study aims to investigate the potential analgesic properties of the crude extract of Monochoria hastata (MH) leaves using in vivo experiments and in silico analysis. The extract, in a dose-dependent manner, exhibited a moderate analgesic property (~54% pain inhibition in acetic acid-induced writhing test), which is significant (** p < 0.001) as compared to the control group. The complex inflammatory mechanism involves diverse pathways and they are inter-connected. Therefore, multiple inflammatory modulator proteins were selected as the target for in silico analysis. Computational analysis suggests that all the selected targets had different degrees of interaction with the phytochemicals from the extract. Rutin (RU), protocatechuic acid (PA), vanillic acid (VA), and ferulic acid (FA) could regulate multiple targets with a robust efficiency. None of the compounds showed selectivity to Cyclooxygenase-2 (COX-2). However, regulation of COX and lipoxygenase (LOX) cascade by PA can reduce non-steroidal analgesic drugs (NSAIDs)-related side effects, including asthma. RU showed robust regulation of cytokine-mediated pathways like RAS/MAPK and PI3K/NF-kB by inhibition of EGFR and IKBα (IKK), which may prevent multi-organ failure due to cytokine storm in several microbial infections, for example, SARS-CoV-2. Further investigation, using in vivo and in vitro experiments, can be conducted to develop multi-target anti-inflammatory drugs using the isolated compounds from the extract.     

Anti-Inflammatory,Antipyretic, and Analgesic Properties of Potamogeton perfoliatus Extract: In Vitro and In Vivo Study

Natural antioxidants, especially those of plant origins, have shown a plethora of biological activities with substantial economic value, as they can be extracted from agro-wastes and/or under exploited plant species. The perennial hydrophyte, Potamogeton perfoliatus, has been used traditionally to treat several health disorders; however, little is known about its biological and its medicinal effects. Here, we used an integrated in vitro and in vivo framework to examine the potential effect of P. perfoliatus on oxidative stress, nociception, inflammatory models, and brewer’s yeast-induced pyrexia in mice. Our results suggested a consistent in vitro inhibition of three enzymes, namely 5-lipoxygenase, cyclooxygenases 1 and 2 (COX-1 and COX-2), as well as a potent antioxidant effect. These results were confirmed in vivo where the studied extract attenuated carrageenan-induced paw edema, carrageenan-induced leukocyte migration into the peritoneal cavity by 25, 44 and 64% at 200, 400 and 600 mg/kg, p.o., respectively. Moreover, the extract decreased acetic acid-induced vascular permeability by 45% at 600 mg/kg, p.o., and chemical hyperalgesia in mice by 86% by 400 mg/kg, p.o., in acetic acid-induced writhing assay. The extract (400 mg/kg) showed a longer response latency at the 3 h time point (2.5 fold of the control) similar to the nalbuphine, the standard opioid analgesic. Additionally, pronounced antipyretic effects were observed at 600 mg/kg, comparable to paracetamol. Using LC-MS/MS, we identified 15 secondary metabolites that most likely contributed to the obtained biological activities. Altogether, our findings indicate that P. perfoliatus has anti-inflammatory, antioxidant, analgesic and antipyretic effects, thus supporting its traditional use and promoting its valorization as a potential candidate in treating oxidative stress-associated diseases.     

A Novel Norlignan and a Novel Phenylpropanoid from Peperomia tetraphylla

A novel cyclobutane‐type norlignan, peperotetraphin (=methyl rel‐(1R,2S,3S)‐2,3‐bis(7‐methoxy‐1,3‐benzodioxol‐5‐yl)cyclobutanecarboxylate; 1 ), and a novel phenylpropanoid, i.e., methyl (2E)‐3‐(7‐methoxy‐1,3‐benzodioxol‐5‐yl)prop‐2‐enoate ( 2 ), along with three known compounds, α‐asarone (=1,2,4‐trimethoxy‐5‐[(1E)‐prop‐1‐en‐1‐yl]benzene), vanillic acid (=4‐hydroxy‐3‐methoxybenzoic acid), and veratric acid (=3,4‐dimethoxybenzoic acid), were isolated from the EtOH extract of the whole plant of Peperomia tetraphylla. Their structures were determined by spectroscopic methods, especially 1D‐ and 2D‐NMR techniques. This is the first report of naturally occurring cyclobutane‐type norlignans.     

Hydrolyzed Flavonoids from Cyrtosperma johnstonii with Superior Antioxidant,Antiproliferative, and Anti-Inflammatory Potential for Cancer Prevention

Cyrtosperma johnstonii is one of the most interesting traditional medicines for cancer treatment. This study aimed to compare and combine the biological activities related to cancer prevention of the flavonoid glycosides rutin (RT) and isorhamnetin-3-o-rutinoside (IRR) and their hydrolysis products quercetin (QT) and isorhamnetin (IR) from C. johnstonii extract. ABTS and MTT assays were used to determine antioxidant activity and cytotoxicity against various cancer cells, as well as normal cells. Anti-inflammatory activities were measured by ELISA. The results showed that the antioxidant activities of the compounds decreased in the order of QT > IR > RT > IRR, while most leukemia cell lines were sensitive to QT and IR with low toxicity towards PBMCs. The reduction of IL-6 and IL-10 secretion by QT and IR was higher than that induced by RT and IRR. The combination of hydrolysis products (QT and IR) possessed a strong synergism in antioxidant, antiproliferative and anti-inflammatory effects, whereas the combination of flavonoid glycosides and their hydrolysis products revealed antagonism. These results suggest that the potential of the combination of hydrolyzed flavonoids from C. johnstonii can be considered as natural compounds for the prevention of cancer.     

Anti-Inflammatory and Anti-Diabetic Effect of Black Soybean Anthocyanins: Data from a Dual Cooperative Cellular System

Obesity is characterized by elevated infiltration of macrophages into adipose tissue, leading to the development of insulin resistance. The black soybean seed coat is a rich source of anthocyanins with antioxidative and anti-inflammatory activities. This study investigated the effects of black soybean anthocyanin extract (BSAn) on obesity-induced oxidative stress, the inflammatory response, and insulin resistance in a coculture system of hypertrophied 3T3-L1 adipocytes and RAW264 macrophages. Coculture of adipocytes with macrophages increased the production of reactive oxygen species and inflammatory mediators and cytokines (NO, MCP-1, PGE₂, TNFα, and IL-6) and the release of free fatty acids but reduced anti-inflammatory adiponectin secretion. BSAn treatment (12.5, 25, 50, and 100 μg/mL) alleviated the coculture-induced changes (p < 0.001) and inhibited coculture-induced activation of JNK and ERK signaling (p < 0.01). BSAn also blocked the migration of RAW264.7 macrophages toward 3T3-L1 adipocytes. In addition, treatment with BSAn increased PPARγ expression and glucose uptake in response to insulin in hypertrophied 3T3-L1 adipocyte and RAW264.7 macrophage coculture (p < 0.01). These results demonstrate that BSAn attenuates inflammatory responses and improves adipocyte metabolic function in the coculture of hypertrophied 3T3-L1 adipocytes and RAW264.7 macrophages, suggesting the effectiveness of BSAn for obesity-induced insulin resistance.     

Ypsilactosides A and B,Two New C22‐Steroidal Lactone Glycosides from Ypsilandra thibetica

Two new C₂₂‐steroidal lactone glycosides, ypsilactosides A ( 1 ) and B ( 2 ), were isolated from the EtOH extract of the whole plant of Ypsilandra thibetica. Their structures were established as (3β,5α,16β,20S)‐3,16‐dihydroxy‐6‐oxopregnane‐20‐carboxylic acid γ‐lactone 3‐(β‐D ‐glucopyranoside) ( 1 ) and (3β,16β)‐3,16‐dihydroxypregna‐5,20‐diene‐20‐carboxylic acid γ‐lactone 3‐{O‐α‐L ‐rhamnopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→4)‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)]‐β‐D ‐glucopyranoside} ( 2 ) on the basis of extensive spectroscopic analyses and chemical degradations.